Download PDF
Synthesis 1994; 1994(12): 1327-1330
DOI: 10.1055/s-1994-25689
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Iron-Mediated Complete Chirality Transfer in Allylic Substitutions. Efficient Synthesis of (-)-(S)-Myoporone

D. Enders* , B. Jandeleit
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, 52074 Aachen, Germany
Further Information

Publication History

Publication Date:
25 April 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

The furanosesquiterpenoid (-)-(S)-myoporone [(S)-10], a toxic stress metabolite of sweet potatoes (Ipomoea batatas) and normal secondary metabolite of the australian shrub Myoporum deserti has been synthesized in high enantiomeric purity (ee > 99 %) and excellent overall yield. Key step in the synthesis is the regio- and stereocontrolled addition of the silyl enol ether 3 to the planar chiral tetracarbonyliron(1+) complex (1R,2S,3R)-2 easily obtained from (S)-lactic acid.

      >